CN115888701B - Catalyst for preparing L-aminopropanol by catalytic hydrogenation and preparation method and application thereof - Google Patents
Catalyst for preparing L-aminopropanol by catalytic hydrogenation and preparation method and application thereof Download PDFInfo
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Abstract
The application relates to the technical field of organic synthesis, in particular to a catalyst for preparing L-aminopropanol by catalytic hydrogenation, a preparation method and application thereof. The preparation method of the catalyst adopts the following steps: and (3) carrying out hot melting on metal ruthenium, alkali and alkali metal nitrate for 2-6 hours at 600-900 ℃, cooling the hot melt, leaching with water to obtain a leaching solution, mixing the leaching solution with a catalyst carrier or aqueous dispersion thereof, reducing with a reducing agent, separating and drying to obtain the catalyst. The catalyst is used for high-efficiency catalytic synthesis of L-aminopropanol by L-alanine, and can effectively improve synthesis yield and product purity.
Description
Technical Field
The application relates to the technical field of organic synthesis, in particular to a catalyst for preparing L-aminopropanol by catalytic hydrogenation, a preparation method and application thereof.
Background
Ofloxacin is a third generation quinolone antibacterial agent which includes levofloxacin and dextrorotatory ofloxacin, wherein dextrorotatory ofloxacin is little helpful for treatment, but adverse reactions are obviously increased. L-aminopropanol is an important intermediate for synthesizing levofloxacin, and is critical for preparing high-purity levofloxacin by providing L-aminopropanol with high chiral purity.
At present, the preparation of L-aminopropanol mainly adopts a chiral resolution method and an L-alanine catalytic hydrogenation method, wherein the chiral resolution method is to prepare DL-aminopropanol firstly and then adopts a chiral resolution reagent to obtain L-aminopropanol, and the method has the problems of complex process and poor atomic economy. The L-alanine catalytic hydrogenation method takes L-alanine as a raw material, and L-aminopropanol is obtained through catalytic hydrogenation, the method avoids the use of chiral resolution reagents, so that the process route is simplified, but the L-alanine catalytic hydrogenation process can also lead to the generation of D-aminopropanol and other side reactions, and the obtained L-aminopropanol product has different contents of D-aminopropanol and other impurities, so that the method is very important for optimizing the catalytic process of the L-alanine catalytic hydrogenation method. Chinese patent CN101298050A discloses a catalyst for synthesizing L-aminopropanol by catalytic hydrogenation, which is prepared by taking copper chloride and ferric chloride as raw materials, taking active carbon as a load body to prepare a modified load body, suspending the modified load body by adopting a surfactant to prepare a suspension, and reducing ruthenium chloride and palladium chloride by adopting formaldehyde as a reducing agent to obtain the catalyst. Also disclosed in this prior art example 4 is a process for the preparation of L-2-aminopropanol by catalytic hydrogenation with the above catalyst: l-2-alanine is used as a raw material, the catalyst is used for preparing L-2-aminopropanol by catalytic hydrogenation at 160 ℃ in an autoclave, and the L-2-aminopropanol with the GC content of 99.8% can be obtained, and the product yield is 79%. Based on the above, it is important to provide a novel catalyst for preparing L-aminopropanol by catalytic hydrogenation of L-alanine and a preparation method thereof to further improve the purity and yield of L-aminopropanol.
Disclosure of Invention
Aiming at the defects of the prior art, the application aims to provide a catalyst for preparing L-aminopropanol by catalytic hydrogenation, a preparation method and application thereof, wherein the catalyst is used for synthesizing the L-aminopropanol by catalytic synthesis of L-alanine, and has higher yield and product purity.
In order to achieve the above purpose, the application adopts the following technical scheme:
the application provides a preparation method of a catalyst for preparing L-aminopropanol by catalytic hydrogenation, which comprises the following steps: and (3) carrying out hot melting on metal ruthenium, alkali and alkali metal nitrate for 2-6 hours at 600-900 ℃, cooling the hot melt, leaching with water to obtain a leaching solution, mixing the leaching solution with a catalyst carrier or aqueous dispersion thereof, reducing with a reducing agent, separating and drying to obtain the catalyst.
Further, the temperature of the hot melting is 750-900 ℃.
Further, the time of the hot melting is 3-4 hours.
Further, the mass ratio of the metallic ruthenium, the base and the alkali metal nitrate is 1:5-20:1-4.
Further, the alkali is at least one selected from alkali metal hydroxide, alkali metal carbonate and alkaline earth metal hydroxide;
preferably, the alkali is at least one of sodium carbonate, potassium carbonate, sodium hydroxide and potassium hydroxide;
preferably, the nitrate is at least one of potassium nitrate and sodium nitrate.
Further, in the leaching step, the mass ratio of the hot melt to the water is 1:1-20; the leaching temperature is 50-90 ℃. Preferably, the leaching temperature is 70-90 ℃.
Further, the catalyst carrier is activated carbon; the activated carbon is pretreated before being mixed with the leaching solution, and the pretreatment method is that the activated carbon is treated by adopting an acid solution; specifically, the pretreatment method is as follows: stirring and heating the activated carbon with 10% nitric acid at 90 ℃ for 2 hours, filtering, washing until effluent is neutral, and drying for later use.
Preferably, the preparation method of the activated carbon aqueous dispersion comprises the following steps: mixing the pretreated activated carbon and water according to the mass ratio of 1:5-20.
Further, the mass ratio of the metallic ruthenium to the catalyst carrier is 1-5:100.
Further, the reducing agent is hydrazine hydrate.
The application also provides a catalyst for preparing the L-aminopropanol by catalytic hydrogenation, which is prepared by adopting the method.
The application also provides an application of the catalyst in preparing L-aminopropanol by catalytic hydrogenation, which comprises the following steps: under the acidic condition, the L-alanine and hydrogen are subjected to catalytic hydrogenation reaction in the presence of a catalyst, and the L-aminopropanol is separated from the reaction product.
Further, the reaction temperature of the catalytic hydrogenation is 80-100 ℃, preferably, the reaction temperature of the catalytic hydrogenation is 80-85 ℃. The reaction pressure of the catalytic hydrogenation is 6-7.5MPa.
Compared with the prior art, the application has the beneficial effects that:
1. the catalyst provided by the application adopts metallic ruthenium, strong alkali and alkali metal nitrate to obtain soluble ruthenate under high-temperature melting condition, and the soluble ruthenate is subjected to water leaching, loading and reduction to obtain the ruthenium catalyst, and the obtained ruthenium catalyst is used for preparing L-aminopropanol by catalytic hydrogenation of L-alanine, and has the advantage of high reaction yield, and the GC purity of the product can reach more than 99.9%.
2. The catalyst provided by the application is used for preparing the L-aminopropanol by catalytic hydrogenation of the L-alanine, can be recycled repeatedly, and can still well maintain the catalytic activity after being used for 200 times.
3. The method for preparing the L-aminopropanol by the catalytic hydrogenation of the L-alanine provided by the application has the advantages that the reaction temperature required by the hydrogenation catalysis is low, the hydrogenation catalysis can be carried out at 80-100 ℃, the production energy consumption can be greatly reduced, and the method has a good industrial application prospect.
Detailed Description
The technical solutions of the present application will be clearly and completely described below in conjunction with the embodiments of the present application, and the described embodiments are only some embodiments of the present application, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to be within the scope of the application.
The methods are conventional methods unless otherwise specified, and the starting materials are commercially available from the public sources unless otherwise specified. The purity of the L-alanine adopted in the embodiment of the application is more than 99 percent, and the concentrations mentioned in the application are mass concentrations unless specified otherwise.
The method for calculating the yield of the application comprises the following steps: yield = weight of desired product formed/weight of theoretical product formed of desired product x 100%.
The method for recycling ruthenium-carbon catalyst in the embodiment of the application comprises the following steps: the ruthenium-carbon catalyst separated from the reaction liquid is boiled for 2 to 3 hours at the temperature of 80 to 90 ℃ by adopting 20 weight percent dilute sulfuric acid, filtered out and boiled for 4 to 5 hours at the temperature of 80 to 90 ℃ by adopting 30 weight percent acetic acid, filtered out and washed by adopting water until the filtrate is neutral, thus obtaining the ruthenium-carbon catalyst.
Example 1
The embodiment provides a preparation method of a catalyst for synthesizing L-aminopropanol by catalytic hydrogenation, which comprises the following steps:
s1, adding 20g of active carbon and 180ml of 10% nitric acid into a 250ml reaction bottle, heating and stirring for 2 hours at 90 ℃, filtering, washing until effluent is neutral, and drying for later use;
s2, putting 1.01g of metal Ru, 11.2g of potassium hydroxide and 1.75g of potassium nitrate into a quartz crucible, putting the quartz crucible into a smelting furnace, heating to 750 ℃ for hot melting for 4 hours, cooling the hot melt to room temperature, carefully transferring the cooled hot melt into a reaction bottle, adding 100g of water into the reaction bottle, heating to 85 ℃, and stirring for 2 hours to obtain a leaching solution;
s3, taking a 1000ml four-neck flask, adding the activated carbon pretreated by the S1 and 200ml water, stirring and dispersing for 10min to obtain an activated carbon aqueous dispersion, adding the leaching solution in the S2, heating to 60 ℃, and dropwise adding 200g of 80% hydrazine hydrate (N) 2 H 4 ·H 2 O) for 30min, and after the dripping, carrying out reflux reaction for 4.5h, cooling, filtering, washing with water, and vacuum drying to obtain the active carbon supported ruthenium catalyst.
Example 2
The embodiment provides a preparation method of a catalyst for synthesizing L-aminopropanol by catalytic hydrogenation, which comprises the following steps:
s1, adding 33g of active carbon and 240ml of 10% nitric acid into a 250ml reaction bottle, heating and stirring for 2 hours at 90 ℃, filtering, washing until effluent is neutral, and drying for later use;
s2, putting 1.01g of metal Ru, 8g of sodium hydroxide and 1.55g of sodium nitrate into a quartz crucible, putting the quartz crucible into a smelting furnace, heating to 800 ℃ for hot melting for 4 hours, cooling the hot melt to room temperature, carefully transferring the cooled hot melt into a reaction bottle, adding 100g of water into the reaction bottle, heating to 70 ℃, and stirring for 2 hours to obtain a leaching solution;
s3, taking a 1000ml four-neck flask, adding the activated carbon pretreated by the S1 and 200ml water, stirring and dispersing for 10min to obtain an activated carbon aqueous dispersion, adding the leaching solution in the S2, heating to 50 ℃, and dropwise adding 200g of 80% hydrazine hydrate (N) 2 H 4 ·H 2 O) for 30min, and after the dripping, carrying out reflux reaction for 4.5h, cooling, filtering, washing with water, and vacuum drying to obtain the active carbon supported ruthenium catalyst.
Example 3
The embodiment provides a preparation method of a catalyst for synthesizing L-aminopropanol by catalytic hydrogenation, which comprises the following steps:
s1, adding 25g of active carbon and 180ml of 10% nitric acid into a 250ml reaction bottle, heating and stirring for 2 hours at 90 ℃, filtering, washing until effluent is neutral, and drying for later use;
s2, putting 1.01g of metal Ru, 14.8g of sodium carbonate and 2.9g of sodium nitrate into a quartz crucible, putting the quartz crucible into a smelting furnace, heating to 800 ℃ for hot melting for 3 hours, cooling the hot melt to room temperature, carefully transferring the cooled hot melt into a reaction bottle, adding 150g of water into the reaction bottle, heating to 90 ℃, and stirring for 2 hours to obtain a leaching solution;
s3, taking a 1000ml four-neck flask, adding the activated carbon pretreated by S1 and 200ml water, stirring and dispersing for 10min to obtain an activated carbon aqueous dispersion, adding the leaching solution in S2, heating to 55 ℃, and dropwise adding 200g of 80% hydrazine hydrate (N) 2 H 4 ·H 2 O) for 30min, and after the dripping, carrying out reflux reaction for 4.5h, cooling, filtering, washing with water, and vacuum drying to obtain the active carbon supported ruthenium catalyst.
Example 4
The active carbon supported ruthenium catalyst prepared in example 1 is taken to prepare L-aminopropanol, and the specific steps are as follows:
s1: adding 89g L-alanine and 320g of water into a hydrogenation reaction kettle, adopting 30% dilute sulfuric acid to adjust the pH value of the reaction solution to be less than 1, adding 25g of ruthenium-carbon catalyst, introducing hydrogen, controlling the reaction temperature to be 80 ℃, controlling the reaction pressure to be 7+/-0.5 MPa, and reacting for 6 hours;
and S2, filtering the reaction solution after the reaction is finished to separate out the catalyst, steaming out about half of water from the filtrate, adding sodium hydroxide solid into the filtrate to adjust the pH to 10, adding ethanol with the volume of 2 times to separate out sodium sulfate, filtering to remove the sodium sulfate, and obtaining a mixture mainly comprising L-aminopropanol, water and ethanol, distilling to obtain 70.4g of L-aminopropanol product, wherein the chemical purity of the sample detection is 99.96% (GC method), and the chiral purity of the L-aminopropanol is 99.90% (HPLC method).
S3, recycling the separated ruthenium-carbon catalyst, repeatedly applying the test according to S1-S2 to prepare L-aminopropanol, and recording the yield and GC purity of the L-aminopropanol obtained by each application, wherein the results are shown in the table 1 below.
Example 5
The preparation and repeated use of L-aminopropanol was carried out in the same manner as in example 4, except that the reaction temperature of S1 was 100℃and 70.5g of L-aminopropanol product was obtained by distillation, and the chemical purity was 99.53% by sampling (GC method) and the chiral purity of L-aminopropanol was 99.77% by HPLC method, using the catalyst prepared in example 1.
Example 6
The active carbon supported ruthenium catalyst prepared in example 2 is taken to prepare L-aminopropanol, and the specific steps are as follows:
s1: adding 89g L-alanine and 320g of water into a hydrogenation reaction kettle, adopting 30% dilute sulfuric acid to adjust the pH value of the reaction solution to be less than 1, adding 26.7g of ruthenium-carbon catalyst, introducing hydrogen, controlling the reaction temperature to be 85 ℃, controlling the reaction pressure to be 6.5+/-0.5 MPa, and reacting for 5 hours;
s2, filtering the reaction solution after the reaction is finished to separate out the catalyst, evaporating about half of water from the filtrate, adding sodium hydroxide solid into the filtrate to adjust the pH to 10, adding 1.5 times of methanol to separate out sodium sulfate, filtering to remove the sodium sulfate, obtaining a mixture mainly comprising L-aminopropanol, water and methanol, distilling to obtain 69.9g of L-aminopropanol product, and sampling and detecting the chemical purity to be 99.84% (GC method), wherein the chiral purity of the L-aminopropanol is 99.83% (HPLC method).
S3, recycling the separated ruthenium-carbon catalyst, repeatedly applying the test according to S1-S2 to prepare L-aminopropanol, and recording the yield and GC purity of the L-aminopropanol obtained by each application, wherein the results are shown in the table 1 below.
Example 7
The active carbon supported ruthenium catalyst prepared in example 3 is taken to prepare L-aminopropanol, and the specific steps are as follows:
s1: adding 89g L-alanine and 320g of water into a hydrogenation reaction kettle, adopting 30% dilute sulfuric acid to adjust the pH value of the reaction solution to be less than 1, adding 25g of ruthenium-carbon catalyst, introducing hydrogen, controlling the reaction temperature to be 80 ℃, controlling the reaction pressure to be 7+/-0.5 MPa, and reacting for 6 hours;
and S2, filtering the reaction solution after the reaction is finished to separate out the catalyst, steaming out about half of water from the filtrate, adding sodium hydroxide solid into the reaction solution to adjust the pH to 10, adding ethanol with the volume of 2 times to separate out sodium sulfate, filtering to remove the sodium sulfate, obtaining a mixture mainly comprising L-aminopropanol, water and ethanol, distilling to obtain 61.5g of L-aminopropanol product, sampling and detecting the chemical purity to 98.25% (GC method), and obtaining lower yield without carrying out subsequent application test.
Comparative example 1
(1) Adding 20g of active carbon and 180ml of 10% nitric acid into a 1000ml reaction bottle, heating and stirring for 2h at 90 ℃, filtering, washing until effluent is neutral, drying, adding 200ml of water into the dried active carbon, stirring and dispersing for 10min to obtain an active carbon aqueous dispersion;
(2) A2500 ml four-necked flask was taken, 2.07g of RuCl3.3H2O and 800ml of water were added, and 10ml of 20% hydrochloric acid was added and stirred uniformly. The aqueous dispersion of activated carbon was added thereto, the temperature was raised to 60℃and 200g of 80% hydrazine hydrate (N) was added dropwise 2 H 4 ·H 2 O) dropwise adding for 30min, regulating pH to 9-10 with 10wt% sodium hydroxide, refluxing for 4.5h, cooling, filtering, washing with water, and vacuum drying to obtain the ruthenium-carbon catalyst.
(3) Adding 89g L-alanine and 320g of water into a hydrogenation reaction kettle, adopting 30% dilute sulfuric acid to adjust the pH value of a reaction solution to be less than 1, adding 25g of the ruthenium-carbon catalyst prepared in the step (2), introducing hydrogen, controlling the reaction temperature to be 100 ℃, controlling the reaction pressure to be 8+/-0.5 MPa, and reacting for 6 hours;
(4) After the reaction, the reaction solution was filtered to separate out the catalyst, and after about half of the water was distilled out from the filtrate, sodium hydroxide solid was added thereto to adjust the pH to 10, ethanol was added in an amount of 2 times by volume to precipitate sodium sulfate, and sodium sulfate was removed by filtration to obtain a mixture of mainly L-aminopropanol, water and ethanol, 69.2g of L-aminopropanol was obtained by distillation, the chemical purity was 99.21% (GC method) by sampling detection, and the chiral purity of L-aminopropanol was 99.77% (HPLC method).
(5) The separated catalyst was recovered and regenerated, and repeated experiments were performed to prepare L-aminopropanol by using the processes of steps (3) - (4), and the yield and GC purity of the obtained L-aminopropanol were recorded for each application, and the results are shown in Table 1 below.
Table 1: repeated application test results of examples 4 to 6 and comparative example 1
Note that: "/" means that example 5, example 6 and comparative example 1 were not subjected to the 200 th recovery test.
As can be seen from the table, compared with comparative example 1, the method for preparing L-aminopropanol from L-alanine provided by examples 4-6 of the application has high reaction yield and better catalyst stability, and the GC purity of the L-aminopropanol obtained by repeated application of 20 times can reach more than 99.0%. The GC purity of the product obtained in example 4 is highest, the yield is high, and the catalytic activity is high after the application time reaches 200 times.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present application and not for limiting the same; while the application has been described in detail with reference to the preferred embodiments, those skilled in the art will appreciate that: modifications and equivalents of some of the features of the specific embodiments of the present application may be made, and they are all included in the scope of the present application as claimed.
Claims (9)
1. A method for preparing an L-aminopropanol catalyst by catalytic hydrogenation, which is characterized by comprising the following steps: carrying out hot melting on metal ruthenium, alkali and alkali metal nitrate at 600-900 ℃ for 2-6 hours, cooling the hot melt, leaching with water to obtain leaching solution, mixing the leaching solution with a catalyst carrier or aqueous dispersion thereof, reducing with a reducing agent, separating and drying to obtain the catalyst;
the method for preparing the L-aminopropanol by catalytic hydrogenation by using the catalyst comprises the steps of carrying out catalytic hydrogenation reaction on L-alanine and hydrogen in the presence of the catalyst under an acidic condition, and separating the L-aminopropanol from a reaction product, wherein the reaction temperature of the catalytic hydrogenation is 80-85 ℃; the reaction pressure of the catalytic hydrogenation is 6-7.5MPa;
the mass ratio of the metallic ruthenium to the alkali metal nitrate is 1:5-20:1-4;
the alkali is at least one of sodium hydroxide and potassium hydroxide;
the nitrate is at least one of potassium nitrate and sodium nitrate.
2. The method of claim 1, wherein in the leaching step, the mass ratio of the hot melt to the water is 1:1-20; the leaching temperature is 50-90 ℃.
3. The method of claim 1, wherein the catalyst support is activated carbon; the activated carbon is pretreated before being mixed with the leaching solution, and the pretreatment method is that the activated carbon is treated by adopting an acid solution.
4. A method of preparing an aqueous dispersion of activated carbon according to claim 3, characterized in that the method of preparing the aqueous dispersion of activated carbon comprises: mixing the pretreated activated carbon and water according to the mass ratio of 1:5-20.
5. The method according to claim 1, wherein the mass ratio of the metallic ruthenium to the catalyst carrier is 1-5:100.
6. The method of claim 1, wherein the reducing agent is hydrazine hydrate.
7. A catalyst for preparing L-aminopropanol by catalytic hydrogenation, which is prepared by the preparation method according to any one of claims 1 to 6.
8. The method for preparing L-aminopropanol by catalytic hydrogenation using the catalyst according to claim 7, wherein the method comprises the steps of: under the acidic condition, the L-alanine and hydrogen are subjected to catalytic hydrogenation reaction in the presence of a catalyst, and the L-aminopropanol is separated from the reaction product.
9. The process of claim 8, wherein the catalytic hydrogenation is carried out at a reaction temperature of 80-85 ℃.
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